Effects of tyrosinase activity on the cytotoxicity of 4-S-cysteaminylphenol and N-acetyl-4-S-cysteaminylphenol in melanoma cells

Prezioso, Joseph A.; Epperly, Michael W.; Wang, Nü; Bloomer, William D.

doi:10.1016/0304-3835(92)90092-a

Cited by 43 publications

(23 citation statements)

References 14 publications

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“…Changes in melanin synthesis occur in many disease states and melanoma specifi c anticarcinogenic activity is known to be linked with tyrosinase (EC 1.14.18.1) activity (Prezioso et al, 1992). Tyrosinase is a key enzyme in the melanin biosynthetic pathway and therefore tyrosinase inhibitors are expected to inhibit melanin production.…”

Section: Resultsmentioning

confidence: 99%

Multifunctional cytotoxic agents from Anacardium occidentale

Kubo

Nitoda

Tocoli

et al. 2010

Phytotherapy Research

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The effects of anacardic acids and cardols isolated from the cashew nut and apple Anacardium occidentale (Anacardiaceae) on murine B16-F10 melanoma cells were tested. Although anacardic acids and cardols were found to inhibit tyrosinase, a key enzyme in melanin synthesis, melanogenesis in melanocytes was not suppressed in cultured cells but rather enhanced. Both anacardic acids and cardols exhibited moderate cytotoxicity.

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Section: Resultsmentioning

confidence: 99%

Multifunctional cytotoxic agents from Anacardium occidentale

Kubo

Nitoda

Tocoli

et al. 2010

Phytotherapy Research

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“…Two other prodrugs, 4-S-cysteaminylphenol (4-S-CAP) and N-acetyl-4-S-cysteaminylphenol (N-Ac-4-S-CAP), were shown to inhibit thymidylate synthase and DNA synthesis in various melanoma cells, although the compounds were essentially nontoxic to nonmelanoma cells (Miura et al, 1990;Pankovich et al, 1990;Prezioso et al, 1992a,b) (Table 8). Partial inhibition of the cytotoxicity of these prodrugs was caused by the tyrosinase inhibitor phenylthiourea, indicating an important role for tyrosinase (Prezioso et al, 1992a). 4-S-CAP is metabolized by tyrosinase to 4-S-cysteaminylcatechol, which auto-oxidates to the ultimate toxin dihydro-1,4-benzothiazine-6,7-dione ( Fig.…”

Section: Enzyme-catalyzed Activation Of Prodrugsmentioning

confidence: 99%

Enzyme-Catalyzed Activation of Anticancer Prodrugs

Rooseboom

Commandeur

Vermeulen

2004

Pharmacological Reviews

447

297

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“…The hydroxylation of L-tyrosine, the initial step in melanin synthesis [1], is also the initial step in catecholamine synthesis. Melanoma specific anticarcinogenic activity is also being linked with tyrosinase activity [2]. Melanin pigments are also found in the mammalian brain.…”

Section: Introductionmentioning

confidence: 99%

Effects of Quercetin on Mushroom Tyrosinase and B16-F10 Melanoma Cells

2007

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Abstract:In searching for tyrosinase inhibitors from plants using L-3,4-dihydroxyphenylalanine (L-DOPA) as a substrate, quercetin was found to be partially oxidized to the corresponding o-quinone under catalysis by mushroom tyrosinase (EC 1.14.18.1). Simultaneously, L-DOPA was also oxidized to dopaquinone and both o-quinones were further oxidized, respectively. The remaining quercetin partially formed adducts with dopaquinone through a Michael type addition. In general, flavonols form adducts with dopaquinone as long as their 3-hydroxyl group is free. Quercetin enhanced melanin production per cell in cultured murine B16-F10 melanoma cells, but this effect may be due in part to melanocytotoxicity. The concentration leading to 50% viable cells lost was established as 20 µM and almost complete lethality was observed at 80 µM.

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Effects of tyrosinase activity on the cytotoxicity of 4-S-cysteaminylphenol and N-acetyl-4-S-cysteaminylphenol in melanoma cells

Cited by 43 publications

References 14 publications

Multifunctional cytotoxic agents from Anacardium occidentale

Multifunctional cytotoxic agents from Anacardium occidentale

Enzyme-Catalyzed Activation of Anticancer Prodrugs

Effects of Quercetin on Mushroom Tyrosinase and B16-F10 Melanoma Cells

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